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通过碱促进的γ-硅基-β,γ-环氧丁腈的开环/布鲁克重排/烯丙基烷基化，随后腈阴离子与双亲电试剂进行环化反应，形成官能化碳环。

Formation of functionalized carbocycles via base-promoted ring opening/Brook rearrangement/allylic alkylation of gamma-silyl-beta,gamma-epoxybutanenitrile followed by nitrile anion cyclization with bis-electrophiles.

作者信息

Matsumoto Tatsuya, Masu Hyuma, Yamaguchi Kentaro, Takeda Kei

机构信息

Department of Synthetic Organic Chemistry, Graduate School of Medical Sciences, Hiroshima University, Minami-Ku, Hiroshima 734-8551, Japan.

出版信息

Org Lett. 2004 Nov 11;6(23):4367-9. doi: 10.1021/ol048100n.

DOI:10.1021/ol048100n
PMID:15524485
Abstract

Reaction of gamma-silyl-beta,gamma-epoxybutanenitrile with a base generates an alpha-nitrile carbanion derivative of 4-siloxybut-3-enenitrile, which undergoes reaction with bis-electrophiles such as 1,omega-dihaloalkanes, omega-bromo-alpha,beta-unsaturated esters, and bisenoates to provide highly functionalized carbocycles.

摘要

γ-甲硅烷基-β,γ-环氧丁腈与碱反应生成4-硅氧基-3-丁烯腈的α-腈基碳负离子衍生物，该衍生物与双亲电试剂如1,ω-二卤代烷烃、ω-溴-α,β-不饱和酯和双烯酸酯反应，生成高度官能化的碳环。

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